Concerning the Efficient Conversion of Epoxy Alcohols into Epoxy Ketones Using Dioxiranes

Representative epoxy alcs. are cleanly converted into the corresponding epoxy ketones in high yields by selective oxidn. using dimethyldioxirane and its trifluoro analog under mild conditions. The oxidn. is found to take place leaving the configuration at the epoxy functionality unaffected. The direct oxyfunctionalization of simple cyclic epoxides with the powerful methyl(trifluoromethyl)dioxirane provides another attractive method to access epoxy ketones regioselectively.